House holiday rentals in Middletown

Unique Dutch Barn in the Hudson Valley

The Unique Dutch Barn, is a magnificent property built in the 1800s and well located in the Hudson Valley on historic Westinghouse Farm. The perfect spot if you are here for a wedding, to visit West Point or LEGOLAND, go hiking, skiing or just to sample the local craft breweries and wineries. For art and music lovers Storm King, Dia Beacon and Bethel Woods are near. Whether you come for a creative retreat, or meet up with old friends and family, this expansive space will offer a memorable stay.

Fall Warwick Escape! Farms, Apple Pick, Ren Faire!

Fall is the BEST time to visit Warwick! You'll love this cozy & relaxing newly constructed home in the heart of Warwick's beautiful & historic Bellvale Hamlet. Enjoy the warm decor, great style, all new furniture, plenty of games & game table for pool or ping pong! Less than 10 minutes to Greenwood Lake, hiking, wineries, breweries, restaurants, Warwick Main Street, Bellvale Creamery & more! Nearby Pennings Orchard & Cidery, Legoland, Mountain Creek Resort & Spa. ~1 hr from NYC Permit # 33758

The Wine & Wilderness Hideaway [Cal King •1hr NYC]

*COZY UP IN OUR SUMMER OASIS NOW! Nature’s haven, indulge in seamless spacious single-level living! Minutes away from Mountain Creek Spa & Water park, Warwick wineries, breweries, creameries & apple picking, scenic hiking trails, serene lakes, enchanting parks, & indulgent restaurants. Open concept, Chef's kitchen, Dishwasher, Washer & Dryer, 2 BR, 2 Bath, Cal King bed w primary BR attached to private Bath w soaking tub a retreat to relaxation. Huge patio & fireplace create everlasting memories

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Modern Woodland Retreat, Hudson Valley & Catskills

A dreamy forest retreat wrapped in trees and good light—perfect for couples or families. Lounge on the deck, sip wine by the fire pit, or sleep in under plush bedding. Inside, you’ll find a fully stocked kitchen, organic toiletries, toys, books, and baby gear—all thoughtfully chosen for comfort and ease. Minutes from Beacon, New Paltz, and Harriman State Park for hikes, river towns, swimming holes, farmers markets, and slow mornings that stretch into golden afternoons.

Millionaire Mansion Countryside Stay w/ Lrg Hottub

You'll be staying in a millionare mansion in the town where cream cheese was invented. Immerse in the fresh upstate NY nature nearby farms! Sugarloaf antique village, famous vineyards, luxury shopping, amusement parks, hiking, swimming, and restaurants. Surround yourself with mountain views through floor-to-ceiling windows spilling shimmering light into spacious rooms. Every room flows effortlessly into the next, naturally creating the space for deep connections.

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Farmhouse Fantasy!

Welcome to your Farmhouse Fantasy! Come enjoy a weekend in the country, just two hours from NYC. Built in 1900, the home was recently gut renovated and features two spacious bedrooms, full bathroom, open plan dining room and living space, a three-season sun room, back deck, and a modern and well appointed kitchen. Located just minutes from Minnewaska State Park and all the beauty and fun the Shawangunks have to offer!

Luxury Mountain Retreat Condo - Skiing & More!

Newly renovated upper level 2 bedroom 2 full bath condo located in Great Gorge Village in Vernon, NJ. Enjoy the beautiful views and create memories in our cozy condo. In close proximity to Mountain Creek resort where there is skiing, snowboarding, waterparks/rides, and mountain biking. Close to Crystal Spring as well with award winning golf courses. Up the road from Minerals Resort.